Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A cozy sleeping area is defined by a soft white bed adorned with decorative pillows. Warm light is provided by unique hanging fixtures. A wooden table displays an arrangement of fruits and snacks alongside elegant candle holders, creating a welcoming and intimate setting.
Tower in Pleasant Hill
4.9 out of 5 average rating, 218 reviews

Kick Cancers Ass With A Stay

Unique. For a Cause. Fun. A place where your stay truly counts! Your stay… Enjoy a night(s) away in an old grain elevator silo that now is home to a fully open concept layout with the most comfortable bed, a soaking tub of your dreams, handmade exposed copper piping & every detailed covered for the perfect getaway! The Cause… 20% of every nights stay goes to Pink Ribbon Good helping local ladies fight cancers. On Site… Coffee & Ice Cream Shop Axe Throwing Sand Volleyball Yard Games Boutiques

Top guest favorite
A welcoming deck is highlighted with various seating arrangements, including two chairs and a small table. Lush greenery surrounds the tranquil lake, where well-maintained paths and fire pits are visible along the water's edge, providing a serene outdoor setting.
Home in Greenville
4.91 out of 5 average rating, 200 reviews

18 LakeS, Dead End Lane, DogS, SpaciouS, 1 nightS

Nestled within the serene surroundings of a picturesque lake community, this delightful lake house offers a charming blend of comfort & convenience. Boasting 3 bed,2 baths, a spacious living room & large kitchen. Outdoors you'll find a dock, paddle boat,& 18 lakes to enjoy. Located as the 1st house of 3 on a quiet dead end. Perfect for those looking to enjoy peaceful evenings on the lake. We are happy to welcome dogs for a fee with your stay. 1 night Stays upon REQUEST! 2 fish passes included.

Top guest favorite
Home in Muncie
4.92 out of 5 average rating, 134 reviews

Cozy place next to Cardinal Greenway

Enjoy your stay in Muncie in a spacious two bedroom, one and a half bath right next to a peaceful walking trail. This property is located in a safe and quiet residential neighborhood making it an ideal home for anyone looking for a comfortable place to stay. This home is in a quaint country setting and offers a great amount of space with a large backyard and driveway. Only a 10-minute drive to BSU and IU Health Ball Memorial Hospital. Direct access to the Cardinal Greenway from the backyard.

Guest favorite
Apartment in Muncie
4.91 out of 5 average rating, 161 reviews

Cute Studio in Old West End

Enjoy a budget-friendly experience at this cozy apartment in Muncie's Old West End neighborhood. Close to downtown hotspots and a short hop to BSU/hospital. Perfect for 1-2 guests. Newly renovated and stylish; all art in the apartment is by local artists. *Please note*, there are no exceptions to the “nonrefundable” option if you choose it. Please research our neighborhood before booking - our prices reflect our location in a diverse, populated urban neighborhood that is being revitalized.

Guest favorite
An open-concept living space features a dining table set for four, with polished plates and glasses. A cozy sofa is adjacent to the fireplace, and the kitchen area includes wooden cabinetry and modern appliances. Natural light filters in through large windows, accentuating the wood paneling.
Home in Hartford City
4.92 out of 5 average rating, 204 reviews

Rustic Lake house with HOT TUB and Pool Table

Come relax in your cozy 1978 Lake House! Conveniently located between Muncie and Hartford City-16 min. from Taylor University, 24 min. from Ball State, 10 seconds from the dock! Enjoy the outdoors-Take out the kayaks, go fishing, enjoy the lake, soak up the sights in the hot tub, then end your night with a campfire! Inside-Shoot some pool on the 1800's pool table, pull out a board game with the family, or just relax in the four-season sunroom while watching the sunset. Enjoy Lake Time!

Top guest favorite
Guest suite in Muncie
4.97 out of 5 average rating, 437 reviews

The Eagles Nest, two bedroom retreat.

Peaceful, centrally-located historic 1892 Queen Anne Victorian home. The Eagle's Nest has private entrance, off street parking, 2 bedrooms, furnished suite on the 2nd floor overlooking White River. Walk 0.6 miles to downtown Muncie, less than 2 miles to Ball State Univ. and 2 blocks to the Bob Ross Experience (Minnetrista). Nearby eatery and brewery options. Just 29 steps to 62-mile Cardinal Greenway, longest trail in Indiana. Might see an eagle hunting along the river too. You will love it!

Guest favorite
A spacious living room is enhanced by green walls and natural light from large windows. Comfortable seating is arranged around a rustic coffee table, with a media console displaying a television. A decorative rug adds warmth to the polished wooden floor.
Cottage in Richmond
4.95 out of 5 average rating, 524 reviews

The Cottage on Abington Pike - Earlham College

Charming private cottage (home) on the West edge of Richmond within walking distance to Earlham College. This updated Three bedroom home has one custom full bath (w/Tub) & one half bath. The kitchen has been updated and is on the lower level. Great location. Wooded private rear yard with covered patio. Cardinal Greenway, Gorge Trail all of Richmond nearby. Fast Wi-Fi. Large Living room & Game room w/Pinball & Multi-cade. Outside quiet 10:00PM. Parties not allowed. 2 Tvs.

Superhost
The historic brick house is surrounded by snow-covered trees and a neatly trimmed hedge. Warm light emanates from the windows, highlighting the architectural details of the structure. A peaceful winter scene is presented, with a gentle snowfall adding to the tranquil atmosphere.
Cottage in Richmond
4.77 out of 5 average rating, 262 reviews

Quaker Hill Cottage on Gated Estate w/Hiking Trail

Quaker Hill Cottage is a 70 year old home located on a private estate in the historic Quaker Hill Neighborhood. Enjoy the peaceful environment surrounded by mature vegetation and active wildlife. This cozy cottage is only steps away from a trailhead that leads to several nature preserve trails & a beautiful waterfall. The Historic Downtown and Depot Districts are both just a mile away or you can visit Earlham College or explore the Antique Alley nearby.

Guest favorite
Cabin in Economy
4.94 out of 5 average rating, 158 reviews

"The Love Shack" Rustic Cabin Getaway

Cabin and/or camper spot, with 30 amp electric & hydrant water. Cabin has 1 full bed, bunk beds (max 4, bring your own linens, firm mattresses) equipped with AC/heat & mini fridge. Indiana's best keep secret - The Love Shack - nestled down a long lane in between 2 fields in rural Economy Indiana with pond & 3 acres to yourself. Started by my grandpa Tom Bond in 2000 and loved by all that visit. Follow us on social media. 2.5 miles to Cardinal greenway.

Top guest favorite
A well-maintained exterior view of a modest structure featuring a green roof and light-colored siding. The entrance is framed by a wooden deck with a railing, accompanied by landscaped stones and decorative elements, including small sculptures and shrubs. Natural light highlights the inviting entryway.
Farm stay in Greens Fork
4.96 out of 5 average rating, 212 reviews

A country night under the stars!

Get away from it all when you stay under the stars. Join us for a peaceful country stay, close enough to drive to nearby shopping and dining, and far enough to hear the crickets and see the stars. Your cozy place will include a kitchenette, coffee pot, microwave & TV. The dining area inside or on the attached deck, full size bed & full bath with shower. Only 3.9 miles from Interstate 70. Should you choose to use 100-foot zipline to exercise your pet.

Top guest favorite
Apartment in Greenville
4.96 out of 5 average rating, 224 reviews

Cozy one bedroom apartment in a Century old house

This first floor one bedroom apartment is in a quiet neighborhood just 4 blocks from Wayne Hospital, 5 blocks from Darke County Fairgrounds and a short 5 minute walk to Downtown Greenville. It sleep up 4. The living room has a queen size sofa bed. IT has a TV with Spectrum streaming app. WiFi is available. It has a fully equipped kitchen with coffee maker and microwave. Other features include a washer and dryer and free street parking.

Guest favorite
The living area features a spacious sectional sofa, a wooden coffee table, and two accent chairs. A television is positioned on a small stand across from the seating arrangement. Natural light enters through two windows adorned with blinds, illuminating the neutral-toned walls.
Apartment in Greens Fork
4.92 out of 5 average rating, 223 reviews

The Doctor's Inn, a newly renovated apartment.

You will have a great time staying in this newly renovated 2 bedroom, wheel chair accessible bathroom apartment. We have a spacious, open-concept kitchen and livingroom suitable for larger families or even hosting a small gathering or event. Located in the country 1/2 way between Indianapolis, IN and Dayton OH, you will find easy access to I 70. This apartment is pet friendly ($15/night) and is equipped with fenced yards for exercise.

Popular amenities for Winchester vacation rentals

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  2. United States
  3. Indiana
  4. Randolph County
  5. Winchester